To clarify, I like Lee. I've seen Gun Town, I enjoyed it, I know he's a serious filmmaker and I completely believe any cabbage I might kick to him would indeed go into another production (if I had any to give, anyway ). Sorry if it came off conversely.
But I took the question as being in general, not specific to any particular filmmaker. In which case, as said, unless I know the person and/or can be provided proof that my cash is going to what it's supposed to be going to, then no. Not a chance.